The school was originally opened in 1986, with its original school building completed in September 1985. From January to March 1986, the building housed Yishun Town Secondary School, as well as
Yishun Junior College. YSS and YTSS then shifted to YTSS on 29 March 1986. Leong Kah Chong was appointed as YSS's first principal on 1 December 1986. Soh Guan Ba was appointed as YSS's second principal in December 1995. In the same year, Goh Choon Leng was appointed as the fourth principal of YSS. In 2006, YSS celebrated its twentieth anniversary and published "My Yishun: Recounting, Reflecting, Reminiscing". In December 2008, Ng Ngoing Keng was appointed the fifth principal of YSS. To celebrate its 32nd Anniversary, YSS broke another record of the Largest Logo made out of colouring books on 29 March 2018. With the logo measuring at 6.9 metres by 9.5 metres, the colouring books were then given to the elderly residents of Sree Narayana Mission as a community service. In 2025, Yishun Secondary School installed a gallery named the Yishun Gallery, with the purpose of educating students about the past history of Nee Soon, from being a rural village to becoming a developed town with a proper town plan namely, the Yishun Town Plan first being developed in the 1980s, the school and the development of communities in Yishun, how the HDB flats developed in the 1980s versus the BTOs now jointly served and met different requirements as well as fulfilled different purposes due to the development of differing needs of residents/people over time. ==References==